Monroe, FL Homes

• 

  

  

  /31

  $219,900 Sold Mar 01, 2025

  • 396 Sq Ft
  • $555/SF
  • 254 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2007

  29859 Overseas Hwy Unit 8, Big Pine Key, FL 33043

  Welcome to your tropical paradise retreat on Big Pine Key! This charming tiny home, nestled within an idyllic RV park, offers the perfect blend of comfort, convenience, and island living. As you step inside, you'll be greeted by a cozy yet efficiently designed living space, complete with dining area, living room, kitchen, bedroom and full bathroom. Natural light floods the interior, creating a

  Kathleen Gomez Coldwell Banker Schmitt RE Co. Lower Keys Office

  29859 Overseas Hwy Unit 8, Big Pine Key, FL 33043
• 

  

  

  /19

  Est $869,574 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  221 Cutthroat Dr, Summerland Key, FL 33042

  221 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  

  /49

  $985,000

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

  Panoramic Ocean Views With Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
• 

  

  

  /64

  $1,660,000 Sold Feb 28, 2025

  • 1,551 Sq Ft
  • $1070/SF
  • 16 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1977

  15 W Cooks, Cook Island Key, FL 33043

  Nestled over 11 acres on a semi-private and pristine offshore island, this exceptional property offers the ultimate in privacy and island living. Accessible only by boat, the home sits along a sandy beach with breathtaking open water views and a serene atmosphere. As you enter into the home endless ocean views great you from the large Great Room highlighted by beautiful pine tongue -in-groove

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  15 W Cooks, Cook Island Key, FL 33043
• 

  

  /2

  Est $1,031,711 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft

  27310 W Indies Dr, Summerland Key, FL 33042

  27310 W Indies Dr, Summerland Key, FL 33042
• 

  

  /26

  $399,000

  • 2 Beds
  • 1 Bath
  • 767 Sq Ft

  27942 Snapper Ln, Summerland Key, FL 33042

  Fantastic starter home in the stunning islands of the Florida Keys! This beautifully renovated home comes fully furnished including stainless steel appliances, microwave, 2 beds, dressers, TVs, couches, tables, and dishes. Located in an adorable and quiet community just over 26 miles from Key West. Bring your buyers!

  Nikki Tatum EXP Realty, LLC

  27942 Snapper Ln, Summerland Key, FL 33042
• 

  

  /48

  $940,000 Sold Feb 28, 2025

  • 2,320 Sq Ft
  • $405/SF
  • 184 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1963

  184 Cutthroat Dr, Summerland Key, FL 33042

  Welcome to 184 Cutthroat Drive, a wonderful income producing waterfront home on the peaceful Cudjoe Key. This home is being sold fully furnished and with kayaks! Has a spacious open floor plan with lots of natural light.Main Level (Upstairs):4 bedrooms, split for plenty of privacy2 full bathroomsLarge living, dining area, and kitchen with an open layout and tons of counter space and cabinets, and

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  184 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /61

  Est $1,895,468 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  17153 Buttonwood Dr W, Summerland Key, FL 33042

  17153 Buttonwood Dr W, Summerland Key, FL 33042
• 

  

  /37

  $530,000

  • 3 Beds
  • 2 Baths
  • 972 Sq Ft

  30957 Mercedes Rd, Big Pine Key, FL 33043

  *** REDUCED - WHAT A BARGAIN! *** PEACEFUL and FENCED - Located in a quiet neighborhood on Big Pine Key, this well-maintained 3 bedroom, 2-bath home offers comfortable living both inside and out. Elevated - short stilts with current flood policy at $775/year.Enjoy the new stainless appliances and a metal roof was installed in 2018. Accordion shutters make it a breeze to button up. Just think,

  Donna Pezzi Keller Williams Key West Compass Realty

  30957 Mercedes Rd, Big Pine Key, FL 33043
• 

  

  /29

  $800,000 Sold Feb 27, 2025

  • 828 Sq Ft
  • $966/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  Beautiful open water home with direct ocean access. Completely furnished, ready to rent, future bookings in place. 52 foot concrete seawall with dock posts. Downstairs locked storage for all your fishing gear and what not, open deck for sunning, covered area for grilling and entertaining, fishing off the seawall. Gorgeous sunrise and sunsets. Community offers full service marina, convenience

  Susan Rich Select Properties of NWFL

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
• 

  

  /39

  Est $1,522,515 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  17056 Wahoo Ln, Summerland Key, FL 33042

  17056 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /40

  $300,000

  • Land

  701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042

  Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with new landscaping, pea rock and concrete parking pad and is equipped with full hookups including water, sewer, and 30, and 50 amp electric

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
• 

  

  /38

  $680,000 Sold Feb 27, 2025

  • 1,040 Sq Ft
  • $654/SF
  • 36 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  29842 Journeys End Rd, Big Pine Key, FL 33043

  Located in the sought-after Tropical Key Colony neighborhood, this 2-bedroom, 2-bathroom home features modern updates with spacious living and exceptional privacy, with two sides of the property protected from future development. The updated kitchen includes stainless steel appliances, quartzite countertops, and generous cabinetry, while vaulted ceilings in the kitchen, living, and dining areas

  Tracy Chacksfield Berkshire Hathaway HomeServices Keys Real Estate

  29842 Journeys End Rd, Big Pine Key, FL 33043
• 

  /2

  Est $1,370,908 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,274 Sq Ft

  21082 6th Ave, Summerland Key, FL 33042

  21082 6th Ave, Summerland Key, FL 33042
• 

  

  /78

  $950,000

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  19512 Aztec St, Summerland Key, FL 33042

  Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  19512 Aztec St, Summerland Key, FL 33042
• 

  

  /20

  $190,000 Sold Feb 27, 2025

  • Land

  • 80 Days On Market

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  Dreaming of Paradise? Your Slice of Waterfront Heaven Awaits! Escape to your very own piece of paradise on Little Torch Key, where the turquoise waters of the Florida Keys meet endless possibilities. This prime waterfront vacant lot offers the perfect canvas to create your tropical oasis. Why This Lot is a Must-Have: 1)Breathtaking Views: Wake up to stunning sunrises and relax with mesmerizing

  Tylon Fraley Southeast Realty Equities, Inc

  28587 Peg Leg Rd, Little Torch Key, FL 33042
• 

  

  /81

  Est $1,447,900 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  23041 Snapper Ln, Summerland Key, FL 33042

  23041 Snapper Ln, Summerland Key, FL 33042
• 

  

  /19

  $250,000

  • Land

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

  Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
• 

  

  /20

  $190,000 Sold Feb 27, 2025

  • Land

  • 80 Days On Market

  28597 Peg Leg Rd, Little Torch Key, FL 33042

  Dreaming of Paradise? Your Slice of Waterfront Heaven Awaits! Escape to your very own piece of paradise on Little Torch Key, where the turquoise waters of the Florida Keys meet endless possibilities. This prime waterfront vacant lot offers the perfect canvas to create your tropical oasis. Why This Lot is a Must-Have: 1)Breathtaking Views: Wake up to stunning sunrises and relax with mesmerizing

  Tylon Fraley Southeast Realty Equities, Inc

  28597 Peg Leg Rd, Little Torch Key, FL 33042
• 

  

  /19

  Est $812,492 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22910 Privateer Dr, Summerland Key, FL 33042

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /49

  $1,140,000

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042

  Welcome to your piece of paradise! This stunning high-rise is the largest square footage home in the exclusive gated community of Venture Out on Cudjoe Key. This property embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042
• 

  /2

  $180,000 Sold Feb 26, 2025

  • Land
  • 0.14 Acre
  • $1,285,714 per Acre

  • 92 Days On Market

  0 Lan Guadaloupe Ln, Lower Keys, FL 33042

  Waterfront Tier III land is now available for acquisition in the beautiful Ramrod Key, presenting an excellent opportunity to secure one of the last few remaining vacant lots in this highly desirable area. A prospective buyer may develop a residence that reflects the vibrant lifestyle characteristic of the Florida Keys, known for its stunning sunrises and sunsets. The lot measures 6,000 square

  Chita Parus Realty Club, LLC

  0 Lan Guadaloupe Ln, Lower Keys, FL 33042
• 

  /2

  Est $1,452,719 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  27362 Anguila Ln, Summerland Key, FL 33042

  27362 Anguila Ln, Summerland Key, FL 33042
• 

  

  /16

  $989,999

  • 3 Beds
  • 3 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

  Rayden Vega CASA MIAMI REAL ESTATE

  22961 John Avery Ln, Summerland Key, FL 33042
• 

  

  /14

  $250,000 Sold Feb 24, 2025

  • 6,725 Sq Ft
  • $37/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1975

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  Looking for an affordable entry into the Florida Keys. This 2-bedbroom,1-Bath mobile home. sits on a 50X 90 lot. in Coral Shores of Little Torch Key on the Gulf Side. of US -1. The home is owner occupied perfect for handyman. Weather your looking to have a Keys hideaway or investment property. Located on a plugged canal does not have boating access. There is a public boat ramp nearby. Room to

  Rose Dell Keller Williams Key West Compass Realty

  1639 Pine Channel Dr, Little Torch Key, FL 33042
• 

  

  /17

  Est $760,538 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  19481 Canal Dr, Summerland Key, FL 33042

  19481 Canal Dr, Summerland Key, FL 33042
• 

  

  /45

  $749,999

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  27163 Mariposa Rd, Summerland Key, FL 33042

  Welcome to your slice of paradise in Ramrod Key! This newer built (2018) beautifully maintained single-family home offers 1,488 square feet of comfortable living space, perfectly situated on a spacious 6,000 square foot lot. Featuring 3 bedrooms and 2 bathrooms, this property is ideal for full-time residents, vacationers, or investors seeking a rental opportunity in the Florida Keys.Special

  Jessica Roden Ocean Sotheby's International Realty

  27163 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /15

  $165,000 Sold Feb 24, 2025

  • Land

  • 18 Days On Market

  8 Calico Jack Circle Cir, Verifying, FL 33042

  Great Cudjoe Key Location with good boating access and sunset skies views down the canal. This lot can be purchased with house next door 22837 Calico Jack Circle. Picture a pool, tiki hut, family fun with beautiful Florida Keys waters... See lot survey in documents tab. Property outline in pictures is approximate. There is a possibility of change to AE zone. Reach out for further information.

  Beata Sharpe COLDWELL BANKER VANGUARD REALTY

  8 Calico Jack Circle Cir, Verifying, FL 33042
• 

  /2

  Est $1,939,474 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,440 Sq Ft

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  22542 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /14

  $1,199,900

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  27463 Antigua Rd, Ramrod Key, FL 33042

  This brand-new, pre-construction home offers the perfect blend of island charm and modern comfort, located in the sought-after Breezeswept Beach Estates neighborhood on picturesque Ramrod Key. (Photos are of a previous Build) Custom designed high-end Affinity modular home with 1380 SF under air, super high 9' tall ceilings adorned with Crown moldings throughout the Home. Huge, covered veranda

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  27463 Antigua Rd, Ramrod Key, FL 33042
• 

  

  /20

  $800,000 Sold Feb 24, 2025

  • 1,200 Sq Ft
  • $667/SF
  • 118 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  27370 W Indies Dr, Summerland Key, FL 33042

  On the ocean side of US1 with Captivating sunrise with peak-a-boo ocean views. Prime location on a 40 ft wide canal 60 ft of canal front with quick, easy access to the ocean. Composite dock with step down. Needs some work and updating. Potential!! 3 Bedroom, 2 bath, 1,200 sq ft with laundry closet. Nice, covered patio deck upstairs could be screened in. Gable/hip metal roof. 3 sets of double

  Rose Dell Keller Williams Key West Compass Realty

  27370 W Indies Dr, Summerland Key, FL 33042
• 

  

  /41

  Est $435,610 Not Listed For Sale

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042
• 

  

  /26

  $999,965

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main 369 370 Dr Unit 369, Cudjoe Key, FL 33042

  Boater's Paradise with Expansive Waterfront Views!Rare opportunity to own one of only three double lots in Venture Out on Cudjoe Key! This 2-bedroom, 2-bath home offers unbeatable waterfront living with a newer 70-ft concrete seawall equipped with davits, bumpers, swim ladder, fish cleaning station, and upgraded dock posts and cleats--perfect for accommodating your large boats. Enjoy sweeping

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  701 Spanish Main 369 370 Dr Unit 369, Cudjoe Key, FL 33042
• 

  

  /28

  $598,000 Sold Feb 24, 2025

  • 1,056 Sq Ft
  • $566/SF
  • 185 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1995

  33 E Cahill Ct, Big Pine Key, FL 33043

  This 2-bedroom 2-bathroom 1056 SF home is in Big Pine Key. Has updated bathrooms, flooring and Stainless-steel appliances. Plenty of room to park all your vehicles, trailers, and RV's. The yard is partially fenced and perfect for your pets or kids. The home is also located on a plugged / swimming canal that is perfect for swimming, A large storage shed is located on this low maintenance property.

  Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  33 E Cahill Ct, Big Pine Key, FL 33043
• 

  /2

  Est $2,200,551 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,514 Sq Ft

  16725 Tamarind Rd, Summerland Key, FL 33042

  16725 Tamarind Rd, Summerland Key, FL 33042
• 

  

  /20

  $145,000

  • Land

  BK 7 LT 6 Coral Way, Big Pine Key, FL 33043

  Just three lots in from the open water, this spacious and partially cleared Tier II Lot is nestled within one of the most private blocks in the desirable and serene Doctor's Arm neighborhood of Big Pine Key - in the heart of Key Deer territory, surrounded by nature. This 5200 Sq. Ft. with 50 ft of waterfrontage is on a clear flowthrough canal. Short distance to No Name Pub. This lot has not yet

  Vanessa J Chamizo Coldwell Banker Schmitt Islamorada

  BK 7 LT 6 Coral Way, Big Pine Key, FL 33043
• 

  

  /16

  $165,000 Sold Feb 24, 2025

  • Land

  • 212 Days On Market

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  Great Cudjoe Key Location with good boating access and sunset skies views down the canal. This lot can be purchased with house next door 22837 Calico Jack Circle. Picture a pool, tiki hut, family fun with beautiful Florida Keys waters... See lot survey in documents tab. Property outline in pictures is approximate. There is a possibility of change to AE zone. Reach out for further information.

  Beata Sharpe Coldwell Banker Vanguard Realty

  8 Calico Jack Cir, Cudjoe Key, FL 33042
• 

  

  /27

  Est $1,707,884 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft

  22836 Port Royal Ln, Summerland Key, FL 33042

  22836 Port Royal Ln, Summerland Key, FL 33042
• 

  

  /19

  $145,000

  • Land

  BK 7 LT 5 Coral Way, Big Pine Key, FL 33043

  Just four lots in from the open water, this spacious and partially cleared Tier II Lot is nestled within one of the most private blocks in the desirable and serene Doctor's Arm neighborhood of Big Pine Key - in the heart of Key Deer territory, surrounded by nature. This 5,750 Sq. Ft. with 50 ft of waterfrontage is on a clear flowthrough canal. Short distance to No Name Pub. This lot has not yet

  Vanessa J Chamizo Coldwell Banker Schmitt Islamorada

  BK 7 LT 5 Coral Way, Big Pine Key, FL 33043
• 

  

  /101

  $4,700,000 Sold Feb 21, 2025

  • 3,727 Sq Ft
  • $1261/SF
  • 25 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2007

  29433 Enterprise Ave, Big Pine Key, FL 33043

  Experience the Pinnacle of Coastal Elegance in Big Pine Key!This openwater masterpiece designed by noted architect Glen Gray, is where modern luxury meets tropical serenity. This luxurious 4-bedroom, 4 1/2 -bathroom estate is a testament to impeccable design and indulgent living. Step inside and be greeted by soaring cathedral ceilings, walls of glass, and an open floorplan that flows seamlessly

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  29433 Enterprise Ave, Big Pine Key, FL 33043

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